Find Historic Hotels in Hillsdale, NY

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Our top choices for Hillsdale historic hotels

Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"The room was very clean. The bed, linens & towels were exceptional. All of the staff were wonderful. "
United States
Joyce
$179 nightly
The price is $200
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Red Lion Inn
Property grounds
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,

Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,

Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
Clinton Corners
8.2 out of 10, Very Good, (11)
"The propert my, grounds and location is just charming. Hosts were stellar and welcoming. Accomodations warm and inviting."
United States
Dawn B.
$170 nightly
The price is $192
Dec 13 - Dec 14
Total with taxes and fees
Omega special, Sunday night thru Thursday night 5 NIGHT MINIMUM, 3 miles away,
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
$460 nightly
The price is $505
Dec 13 - Dec 14
Total with taxes and fees
Inn at Kenmore Hall
Property grounds
Private room on secluded 7 acres , access to entire house including patio, porch

Private room on secluded 7 acres , access to entire house including patio, porch

Private room on secluded 7 acres , access to entire house including patio, porch
Clinton Corners
8.6 out of 10, Excellent, (30)
"It was just as advertised! Host was nice included fruit and coffee "
United States
matt w.
$180 nightly
The price is $204
Dec 13 - Dec 14
Total with taxes and fees
Private room on secluded 7 acres , access to entire house including patio, porch
Interior
rural, serene + sophisticated space

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
$303 nightly
The price is $339
Dec 16 - Dec 17
Total with taxes and fees
rural, serene + sophisticated space
Outdoor pool, a heated pool
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Hudson
9.8 out of 10, Exceptional, (27)
"Met our son and his girls for a little getaway. Very cool house complete with lots to do! Thank you. Hope to get to experience it during the summer months sometime."
United States
Kathy M.
$973 nightly
The price is $1,099
Dec 14 - Dec 15
Total with taxes and fees
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillsdale Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there"
Sara 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What should a history buff expect from a stay in Hillsdale?
The historical sites in Hillsdale are probably at the top of your sightseeing list. You can also explore all there is to see and do such as the coffeehouses and ski areas
How many historical hotels will I find in Hillsdale?
Hillsdale is home to 66 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the most important historical sites and other places to visit in Hillsdale?
Favorite places to visit include Catamount Aerial Adventure Park, Catamount Ski Area, and Copake Lake. A couple of additional sights to add to your agenda are Hillsdale Town Hall and Community Library.
What is a historic hotel like in Hillsdale?
Guests who choose a historic hotel can enjoy a vacation someplace that has an official historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be transformed into a historic hotel as long as it's of special interest. Traditional architecture and period features can be admired in the guestrooms or communal spaces of historic hotels in Hillsdale, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. though overall the terms are quite similar. The building and architecture of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value as well as how it influenced the community.
Do historic hotels in Hillsdale have modern facilities?
Hotels have the safety features and modern conveniences you might expect, but every effort is made to preserve treasured traditions and historic facades. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the usual amenities found at a contemporary hotel will be available in a historic hotel. When you choose a historic hotel in Hillsdale, don't worry that you'll be staying at a place that's uncomfortable or rundown.

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